Organocatalytic Asymmetric Nucleophilic Addition to o-Quinone Methides by Alcohols

被引：106

作者：

Lai, Zengwei ^{[1
]}

Wang, Zhaobin ^{[1
]}

Sun, Jianwei ^{[1
]}

机构：

[1] Hong Kong Univ Sci & Technol, Dept Chem, Kowloon, Hong Kong, Peoples R China

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 24期

关键词：

OXY-MICHAEL ADDITION; BRONSTED ACID; ENANTIOSELECTIVE SYNTHESIS; IN-SITU; DIASTEREOSELECTIVE SYNTHESIS; AEROBIC DIALKOXYLATION; CONJUGATE ADDITION; DIRECTING GROUP; ACTIVATION; CATALYSIS;

D O I：

10.1021/acs.orglett.5b03072

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first catalytic asymmetric intermolecular alcohol conjugate addition to o-quinone methides (o-QMs) is disclosed. Due to reversible C-O bond formation and low nucleophilicity of alcohols, catalytic asymmetric oxa-Michael additions with simple alcohol nucleophiles to establish acyclic oxygenated carbon stereocenters remain scarce. The present reaction represents a rare example of this type. With a suitable chiral acid catalyst, the in situ formation of o-QMs and subsequent conjugate addition proceeded with high efficiency and enantioselectivity. The chiral ether products are versatile precursors to other chiral molecules.

引用

页码：6058 / 6061

页数：4

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